HCID 20738641, compound → (4-Amino-3-methoxy-2-methylphenyl)acetonitrile
Reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:15])=[C:5]([CH2:12][C:13]#[N:14])[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O>C(O)C.[Pd]>[NH2:9][C:8]1[CH:7]=[CH:6][C:5]([CH2:12][C:13]#[N:14])=[C:4]([CH3:15])[C:3]=1[O:2][CH3:1]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (3-methoxy-2-methyl-4-nitro-phenyl)-acetonitnle (1.03 g, 5.0 mmole) in ethanol (100 mL) was added a small amount of 10% palladium on charcoal catalyst and the mixture hydrogenated on the Parr hydrogenator at 45 psi for 3.5 hours. The reaction mixture was filtered through celite and evaporated under reduced pressure to give the (4-amino-3-methoxy-2-methyl-phenyl)acetonitrile as a solid (0.912 g, 100%). 1H NMR (CDCl3) δ: 2.25 (s, 3H), 3.56 (s, 2H), 3.72 (s, 3H), 3.85 (br, 2H), 6.60 (d, 1H, J=8.1 Hz), 6.90 (d, 1H, J=8.1 Hz).